NPASS Compound

Natural Product: NPC101825

Natural Product ID	NPC101825
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BJFULXIXCCBDTJ-SWEQPJHZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451077
PubChem CID	24813260
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 105108 0 0 0 0 0 0 0 0999 V2000 9.0612 5.0373 1.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4901 4.7305 -0.2750 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2754 3.2025 -0.3085 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3091 2.8923 0.8135 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0461 1.4215 0.8937 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4464 0.9083 -0.3744 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1327 1.5848 -0.6440 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5566 1.0313 -1.9413 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3646 -0.4381 -1.7901 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4241 -0.7105 -0.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3557 -0.0760 -0.5683 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7196 -1.6425 0.3161 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9202 -1.9785 1.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6602 -2.5835 0.9518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5299 -2.0000 1.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8971 -2.3974 0.9498 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7003 -1.1452 1.0021 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0625 -1.2045 0.5071 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8021 -1.1504 2.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1051 -2.2860 2.9016 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9632 0.2093 2.7090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8735 -0.1558 0.1248 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7141 0.7990 -0.8256 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6808 0.7994 -1.5029 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8384 1.7804 -0.9602 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5979 2.8397 -1.9733 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7994 3.7539 -2.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1358 4.4400 -0.7645 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3534 5.3105 -1.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7889 6.0527 0.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1432 5.0459 1.3022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4131 -2.5298 -0.1194 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3269 -3.1065 -0.9816 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9691 -3.1004 -0.3584 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4184 -4.4668 -0.3810 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7571 -4.7339 0.5189 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8753 -3.8512 0.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4414 -4.7333 1.8743 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9215 -6.1836 0.1659 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9284 -6.8252 -0.0986 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4950 -6.6279 0.2278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2758 -5.6016 -0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9162 -8.0208 0.5964 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1514 -2.3249 -1.2314 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3637 -2.3745 -2.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2003 5.3000 1.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7624 5.9054 1.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6066 4.1443 1.4577 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4986 5.2014 -0.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2091 4.9939 -1.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7793 2.9810 -1.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2268 2.6947 -0.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7753 3.2517 1.7721 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4028 3.5051 0.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9840 0.8551 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3404 1.2355 1.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2414 -0.1970 -0.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1191 1.0941 -1.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1968 2.6807 -0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4201 1.2971 0.1803 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5831 1.4965 -2.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3048 1.1973 -2.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2584 -1.0565 -1.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7787 -0.7744 -2.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6791 -1.1049 2.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4493 -2.7658 2.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6524 -1.0954 1.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1684 -3.0715 1.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1538 -0.1861 0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 -2.2444 3.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 -3.2948 2.5228 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1387 -2.1272 3.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4797 0.9375 2.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9534 0.6615 2.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4654 0.1469 3.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7375 1.2033 -1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0166 2.2748 0.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7308 3.4858 -1.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4676 2.4243 -3.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6880 3.1238 -2.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6762 4.5441 -2.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4487 3.7171 0.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2858 5.0507 -0.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0824 6.0432 -1.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1729 4.6873 -1.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9094 6.6159 0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6707 6.6862 0.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2814 4.7882 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5585 4.1326 0.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9680 5.4575 1.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3036 -2.4203 -0.7822 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7137 -3.3093 0.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6621 -4.1404 -1.2465 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0087 -4.6517 -1.4286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8786 -4.2824 0.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8291 -3.5548 -0.9149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0922 -4.1571 2.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3640 -5.7488 -0.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3857 -8.0394 1.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0621 -8.6968 0.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6607 -8.4117 -0.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0581 -1.4089 -0.9270 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5933 -1.5812 -2.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0050 -3.0488 -3.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3642 -2.0353 -2.5985 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 18 22 1 6 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 18 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 1 36 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 41 43 1 0 34 44 1 6 33 45 1 0 37 14 1 0 34 16 1 0 42 35 1 0 19 17 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 13 65 1 0 13 66 1 0 15 67 1 0 16 68 1 1 17 69 1 6 20 70 1 0 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 25 76 1 0 25 77 1 0 26 78 1 0 26 79 1 0 27 80 1 0 27 81 1 0 28 82 1 0 28 83 1 0 29 84 1 0 29 85 1 0 30 86 1 0 30 87 1 0 31 88 1 0 31 89 1 0 31 90 1 0 32 91 1 0 32 92 1 0 33 93 1 6 35 94 1 6 37 95 1 0 37 96 1 0 38 97 1 0 42 98 1 0 43 99 1 0 43100 1 0 43101 1 0 44102 1 0 45103 1 0 45104 1 0 45105 1 0 M END

Standard InCHIKey	BJFULXIXCCBDTJ-SWEQPJHZSA-N
Standard InCHI	InChI=1S/C38H60O7/c1-7-9-11-13-14-16-17-19-31(39)44-25-28-22-29-33-35(5,6)37(33,45-32(40)20-18-15-12-10-8-2)23-27(4)38(29,43)30-21-26(3)34(41)36(30,42)24-28/h21-22,27,29-30,33,42-43H,7-20,23-25H2,1-6H3/t27-,29+,30-,33-,36-,37+,38-/m1/s1
SMILES	CCCCCCCCCC(=O)OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)CCCCCCC)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	628.43	Volume:	679.927 ? Van der Waals volume.
Dense:	0.924	LogP:	6.789 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.746 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.854 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	21.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.86	Fsp³:	0.816
MCE-18:	75.565 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.546	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.467

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.184	MDCK Permeability:	-4.743
Pgp-inhibitor:	0.005	Pgp-substrate:	0.377
PAMPA:	0.528 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.997
Plasma Protein Binding (PPB):	97.488%	Volume Distribution (VD):	0.498
Fu:	2.987% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.025
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.018	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.966 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.09

Half-life (T1/2):

0.881

ADMET: Toxicity

hERG Blockers:	0.287	hERG Blockers (10um):	0.692
Human Hepatotoxicity (H-HT):	0.5	Drug-induced Liver Injury (DILI):	0.498
AMES Toxicity:	0.299	Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.609	Skin Sensitization:	0.996
Carcinogencity:	0.824	Eye Corrosion:	0.02
Eye Irritation:	0.598	Respiratory Toxicity:	0.848
Drug-induced Neurotoxicity:	0.052	Ototoxicity:	0.372
Hematotoxicity:	0.295	Drug-induced Nephrotoxicity:	0.92
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.188
A549 Cytotoxicity:	0.611	Hek293 Cytotoxicity:	0.374
BCF:	1.55 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.069 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.487 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.477 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Activity	9
Inhibition	3
Ratio	2

Activity Type	# Activity
Cell line	15

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[11831887]
NPT91	Cell line	KB	Homo sapiens	Activity	=	74.69	%	PMID[19226154]
NPT91	Cell line	KB	Homo sapiens	Activity	=	65.0	%	PMID[26394911]
NPT91	Cell line	KB	Homo sapiens	Activity	=	26.11	%	PMID[21705225]
NPT91	Cell line	KB	Homo sapiens	Activity	=	25.23	%	PMID[25688575]
NPT91	Cell line	KB	Homo sapiens	Activity	=	34.0	%	PMID[23398362]
NPT91	Cell line	KB	Homo sapiens	Activity	=	70.89	%	PMID[20704301]
NPT91	Cell line	KB	Homo sapiens	Activity	=	0.0	%	PMID[20704301]
NPT91	Cell line	KB	Homo sapiens	Activity	=	1.0	%	PubChem BioAssay data set
NPT91	Cell line	KB	Homo sapiens	Activity	=	3.0	%	PubChem BioAssay data set
NPT91	Cell line	KB	Homo sapiens	Inhibition	=	74.69	%	PMID[17296745]
NPT91	Cell line	KB	Homo sapiens	Ratio	=	0.87	n.a.	PMID[21109433]
NPT91	Cell line	KB	Homo sapiens	Inhibition	=	85.0	%	PubChem BioAssay data set
NPT91	Cell line	KB	Homo sapiens	Ratio	=	0.71	n.a.	PMID[20704301]
NPT91	Cell line	KB	Homo sapiens	Inhibition	=	23.0	%	PMID[20575572]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC101825 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	16004
0.1-0.2	32210
0.2-0.3	1505
0.3-0.4	59
0.4-0.5	29
0.5-0.6	20
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17138
1.0	High Similarity	NPC215643
1.0	High Similarity	NPC265499
0.9836	High Similarity	NPC221511
0.9355	High Similarity	NPC170212
0.8788	High Similarity	NPC151216
0.8788	High Similarity	NPC89227
0.8657	High Similarity	NPC479000
0.7778	Intermediate Similarity	NPC96739
0.7727	Intermediate Similarity	NPC485736
0.7727	Intermediate Similarity	NPC277477
0.7727	Intermediate Similarity	NPC479003
0.7727	Intermediate Similarity	NPC485735
0.7727	Intermediate Similarity	NPC485733
0.7424	Intermediate Similarity	NPC174471
0.7206	Intermediate Similarity	NPC474871
0.7206	Intermediate Similarity	NPC260786
0.6944	Remote Similarity	NPC485731
0.6944	Remote Similarity	NPC485732
0.6364	Remote Similarity	NPC257017
0.6316	Remote Similarity	NPC183540
0.6301	Remote Similarity	NPC482454
0.6282	Remote Similarity	NPC602538
0.6176	Remote Similarity	NPC153036
0.6176	Remote Similarity	NPC91189
0.6125	Remote Similarity	NPC162009
0.6	Remote Similarity	NPC159692
0.6	Remote Similarity	NPC158523
0.5875	Remote Similarity	NPC222307
0.5844	Remote Similarity	NPC475391
0.5833	Remote Similarity	NPC71889
0.5833	Remote Similarity	NPC475937
0.5802	Remote Similarity	NPC153651
0.5696	Remote Similarity	NPC474937
0.5641	Remote Similarity	NPC482317
0.5641	Remote Similarity	NPC477091
0.561	Remote Similarity	NPC472760
0.5526	Remote Similarity	NPC609113
0.5385	Remote Similarity	NPC275696
0.5385	Remote Similarity	NPC255081
0.525	Remote Similarity	NPC603912
0.5125	Remote Similarity	NPC5991
0.5125	Remote Similarity	NPC196500
0.5125	Remote Similarity	NPC471108
0.5125	Remote Similarity	NPC5989
0.5122	Remote Similarity	NPC22628
0.5122	Remote Similarity	NPC600005
0.5065	Remote Similarity	NPC478681

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC101825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6327
0.1-0.2	2762
0.2-0.3	61
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data